Sodium amide → HCID 66848669, compound

HRID 2176107Notes

Reaction equation

HRID 2176107 reaction equation
[NH2-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.Br[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1>O1CCCC1>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][N:10]([C:7]2[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=2)[NH2:11])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 69982(4-Fluorophenyl)hydrazineHCID 5731534-Fluorophenethyl bromide

Product 1

HCID 66848669HCID 66848669, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask containing tetrahydrofuran (6.0 mL; Aldrich) was charged with sodium amide (0.488 g, 11.89 mmol; Acros) and chilled to 0° C. (4-Fluorophenyl)hydrazine (1.0 g, 7.9 mmol; Aldrich) was added in portions. After 5 minutes the solid had completely dissolved. The ice bath was removed and stirring was continued for 1 hour. The solution was chilled again in an ice bath and 1-(2-bromoethyl)-4-fluorobenzene (1.731 ml, 8.72 mmol; Aldrich) was added dropwise. After 10 minutes the ice bath was removed and stirring was continued for 1.5 hours. The mixture was poured into water (5 mL). The tetrahydrofuran was removed under reduce pressure and the residue was diluted with water (20 mL). The aqueous layer was extracted with diisopropyl ether (2×25 mL) and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the title product which was carried on without further purification: MS (DCI/NH3) m/z 248.9 (M+H)+.

Workup

  1. additionwas added in portions
  2. dissolutionAfter 5 minutes the solid had completely dissolved
  3. customThe ice bath was removed
  4. temperatureThe solution was chilled again in an ice bath
  5. customAfter 10 minutes the ice bath was removed
  6. stirringstirring
  7. waitwas continued for 1.5 hours
  8. additionThe mixture was poured into water (5 mL)
  9. customThe tetrahydrofuran was removed
  10. additionthe residue was diluted with water (20 mL)
  11. extractionThe aqueous layer was extracted with diisopropyl ether (2×25 mL)
  12. dry with materialthe combined organic extracts were dried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d73b7ebcc7534d19a059c5fd534fb96a
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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